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Synthesis of 13 C, 14 C and 2 H 13 C labeled adrenoceptor antagonists: 6‐chloro‐2,3,4,5‐tetrahydro‐3‐methyl‐1 H ‐3‐benzazepine hydrochloride and its N‐desmethyl analog
Author(s) -
Villani A. J.,
Etzkorn F.,
Rotert G. A.,
Heys J. R.
Publication year - 1988
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580251208
Subject(s) - chemistry , isotopomers , carbon 14 , carbon 13 , desmethyl , hydrolysis , medicinal chemistry , lithium (medication) , stereochemistry , chemical synthesis , derivative (finance) , radiochemistry , organic chemistry , metabolite , molecule , medicine , biochemistry , economics , financial economics , endocrinology , physics , quantum mechanics , in vitro
The compound 6‐chloro‐2,3,4,5‐tetrahydro‐3‐methyl‐1 H ‐3‐benzazepine (SK&F 86466) was prepared in phenyl‐U‐ 14 C and phenyl‐ 13 C 6 labeled forms in a six step sequence beginning with the appropriately labeled benzenes. In addition, the N‐desmethyl analog of the carbon‐14 labeled isotopomer and the N‐methyl‐ 2 H 3 derivative of the carbon‐13 isotopomer were prepared via the N‐(2,2,2‐trichloroethyl) carbamates by hydrolysis and lithium aluminum deuteride reduction, respectively.